EP2590025A1 - Composition de résine photosensible, pellicule de composition de résine photosensible, et dispositif semi-conducteur utilisant la composition de résine photosensible ou la pellicule de composition de résine photosensible - Google Patents

Composition de résine photosensible, pellicule de composition de résine photosensible, et dispositif semi-conducteur utilisant la composition de résine photosensible ou la pellicule de composition de résine photosensible Download PDF

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Publication number
EP2590025A1
EP2590025A1 EP11800602.2A EP11800602A EP2590025A1 EP 2590025 A1 EP2590025 A1 EP 2590025A1 EP 11800602 A EP11800602 A EP 11800602A EP 2590025 A1 EP2590025 A1 EP 2590025A1
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EP
European Patent Office
Prior art keywords
resin composition
photosensitive resin
polyimide
compound
film
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP11800602.2A
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German (de)
English (en)
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EP2590025B1 (fr
EP2590025A4 (fr
Inventor
Hiroyuki Niwa
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Toray Industries Inc
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Toray Industries Inc
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Publication of EP2590025A4 publication Critical patent/EP2590025A4/fr
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1042—Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1046—Polyimides containing oxygen in the form of ether bonds in the main chain
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1057—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain
    • C08G73/106—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain containing silicon
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    • C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
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    • C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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Definitions

  • the present invention relates to a photosensitive resin composition and a photosensitive resin composition film. More particularly, the present invention relates to a photosensitive composition that is used for a semiconductor element, a semiconductor device having multilayer structure, a photosensitive composition such as an image sensor and so on, particularly a photosensitive resin composition having an adhesion function.
  • the adhesive used here preferably has such a photosensitivity that an adhesive on an electrode can be removed by patterning for exposing an electrode part to secure conduction between chips, in addition to properties prerequisite for assembly reliability such as a low stress property, adhesion, an insulating property and such a heat resistance that reflow soldering can be endured.
  • an alkali-soluble polyimide has high thermal stress, and exhibits an insufficient thermocompression property to a support substrate such as a silicon wafer or a glass substrate in some cases.
  • the material is a negative tone photosensitive material, and the pattern shape tends to be an inverse tapered shape.
  • the positive tone photosensitive materials described in Patent Documents 4 and 5 do not have a sufficient adhesion function, and are difficult to be formed into a B stage sheet and used because a film after drying off a solvent is fragile.
  • An object of the present invention is to provide a positive tone photosensitive resin composition and photosensitive resin composition film, each of which has small stress after curing and exhibits excellent adhesion.
  • the present invention is a photosensitive resin composition containing: (a) an alkali-soluble polyimide which has a structural unit represented by general formula (1), while having a structure represented by general formula (2) and/or (3) at at least one end of the main chain; (b) a compound which has two or more epoxy groups and/or oxetanyl groups in each molecule; and (c) a naphthoquinonediazide compound, wherein the content of the compound (b) is not less than 20 parts by weight per 100 parts by weight of the polyimide (a).
  • a photosensitive resin composition and a photosensitive resin composition film each of which is capable of forming a positive tone pattern by photolithography, has small stress after curing, and exhibits a high strength of adhesion with a semiconductor element and a support member.
  • a photosensitive resin composition of the present invention contains (a) an alkali-soluble polyimide which has a structural unit represented by general formula (1), while having a structure represented by general formula (2) and/or (3) at at least one end of the main chain; (b) a compound which has two or more epoxy groups and/or oxetanyl groups in each molecule; and (c) a naphthoquinonediazide compound, wherein the content of the compound (b) is not less than 20 parts by weight per 100 parts by weight of the polyimide (a).
  • the polyimide as component (a) is an alkali-soluble polyimide.
  • alkali-soluble used herein means that the solubility in a 2.38% aqueous tetramethyl ammonium solution is not less than 0.1g/100 mL.
  • alkali-soluble used herein means that the solubility in a 2.38% aqueous tetramethyl ammonium solution is not less than 0.1g/100 mL.
  • the polyimide as component (a) has a structural unit represented by general formula (1) below, while having a structure represented by general formula (2) and/or (3) at at least one end of the main chain.
  • X represents a monovalent organic group having at least one selected from the group consisting of a carboxyl group, a phenolic hydroxyl group, a sulfonic acid group and a thiol group
  • Y represents a divalent organic group having at least one selected from the group consisting of a carboxyl group, a phenolic hydroxyl group, a sulfonic acid group and a thiol group
  • X is preferably an aromatic group
  • Y is preferably an aromatic group, or a group having a carbon-carbon double bond.
  • X and Y preferably have a phenolic hydroxyl group or a thiol group.
  • R 1 represents a tetra- to tetradeca-valent organic group
  • R 2 represents a di- to dodeca-valent organic group
  • R 3 and R 4 each independently represent at least one group selected from the group consisting of a carboxyl group, a phenolic hydroxyl group, a sulfonic acid group and a thiol group.
  • ⁇ and ⁇ each independently represent an integer of 0 to 10.
  • R 1 represents a structural component derived from a tetracaboxylic dianhydride. Particularly, it is preferably an organic group containing an aromatic group or a cyclic aliphatic group and having 5 to 40 carbon atoms.
  • tetracarboxylic dianhydride examples include aromatic tetracarboxylic dianhydrides such as pyromellitic dianhydride, 3,3',4,4'-biphenyltetracarboxylic dianhydride, 2,3,3',4'-biphenyltetracarboxylic dianhydride, 2,2',3,3'-biphenyltetracarboxylic dianhydride, 3,3',4,4'-benzophenonetetracarboxylic dianhydride, 2,2',3,3'-benzophenonetetracarboxylic dianhydride, 2,2-bis(3,4-dicarboxyphenyl)propane dianhydride, 2,2-bis(2,3-dicarboxyphenyl)propane dianhydride, 1,1-bis(3,4-dicarboxyphenyl)ethane dianhydride, 1,1-bis(2,3-dicarboxyphenyl)ethane dian
  • R 9 represents a group selected from an oxygen atom, C(CF 3 ) 2 , C(CH 3)2 , CO, COO and SO 2
  • R 10 and R 11 each represent a group selected from a hydrogen atom, a hydroxyl group and a thiol group.
  • R 2 represents a structural component derived from a diamine. Particularly, it is preferably an organic group containing an aromatic group or a cycloaliphatic group and having 5 to 40 carbon atoms.
  • diamine examples include 3,3'-diaminodiphenyl ether, 3,4'-diaminodiphenyl ether, 4,4'-diaminodiphenyl ether, 3,3'-diaminodiphenyl methane, 3,4'-diaminodiphenyl methane, 4,4'-diaminodiphenyl methane, 3,3'-diaminodiphenyl sulfone, 3,4'-diaminodiphenyl sulfone, 4,4'-diaminodiphenyl sulfone, 3,4'-diaminodiphenyl sulfide, 4,4'-diaminodiphenyl sulfide, 1,4-bis(4-aminophenoxy)benzene, 1,3-bis(4-aminophenoxy)benzene, 1,3-bis(3-aminophenoxy)benzene, benzidine
  • R 9 represents a group selected from an oxygen atom, C(CF 3 ) 2 , C(CH 3)2 , CO, COO and SO 2
  • R 10 and R 13 each represent a group selected from a hydroxyl group and a thiol group.
  • R 9 represents a group selected from an oxygen atom, C(CF 3 ) 2 , C(CH 3)2 , and SO 2
  • R 10 and R 13 each represent a group selected from a hydroxyl group and a thiol group.
  • R 3 and R 4 each independently represent at least one selected from the group consisting of a carboxyl group, a phenolic hydroxyl group, a sulfonic acid group and a thiol group.
  • an aliphatic group having a siloxane structure may be copolymerized with R 2 within the bounds of not reducing the heat resistance.
  • the diamine component include those obtained by copolymerizing 1 to 10 mol% of bis(3-aminopropyl)tetramethyl disiloxane, bis(p-amino-phenyl)octamethyl pentasiloxane and so on.
  • General formulae (2) and (3) show the structure of the end of a polyimide having a structural unit represented by general formula (1).
  • the polyimide have two ends, at least one of which should have a structure represented by general formula (2) and/or (3).
  • a polyimide having a structure represented by general formula (2) and/or (3) at the end of the main chain can be synthesized using a publicly known method with a part of a diamine replaced by a monoamine which is an end capping agent, or with a tetracarboxylic dianhydride replaced by a dicarboxylic anhydride which is an end capping agent.
  • a polyimide precursor is obtained by, for example, a method in which a tetracarboxylic dianhydride, a diamine compound and a monoamine are reacted at a low temperature, a method in which a tetracarboxylic dianhydride, a dicarboxylic anhydride and a diamine compound are reacted at a low temperature, or a method in which a diester is obtained by a tetracarboxylic dianhydride and an alcohol, and then reacted with a diamine and a monoamine in the presence of a condensation agent. Thereafter, a polyimide can be synthesized by imidizing the obtained polyimide precursor by a publicly known imidization reaction.
  • X is derived from a primary monoamine which is an end capping agent.
  • the primary monoamine used as an end capping agent 5-amino-8-hydroxyquinoline, 1-hydroxy-7-aminonaphthalene, 1-hydroxy-6-aminonaphthalene, 1-hydroxy-5-aminonaphthalene, 1-hydroxy-4-aminonaphthalene, 2-hydroxy-7-aminonaphthalene, 2-hydroxy-6-aminonaphthalene, 2-hydroxy-5-aminonaphthalene, 1-carboxy-7-aminonaphthalene, 1-carboxy-6-aminonaphthalene, 1-carboxy-5-aminonaphthalene, 2-carboxy-7-aminonaphthalene, 2-carboxy-6-aminonaphthalene, 2-carboxy-5-aminonaphthalene, 2-aminobenzoic acid, 3-aminobenzoic acid, 4-aminobenzoic acid, 4-aminosalicylic acid, 5-aminosalicylic acid, 5-
  • Y is derived from a dicarboxylic anhydride which is an end capping agent.
  • acid anhydride used as an end capping agent 4-carboxyphthalic anhydride, 3-hydroxyphthalic anhydride, cis-aconitic anhydride and so on are preferable. They are used alone or in combination of two or more thereof.
  • the polyimide which has a structural unit represented by general formula (1), while having a structure represented by general formula (2) and/or (3) at at least one of the ends of the main chain, may be one having a repeating unit consisting of only the structural unit represented by general formula (1), or may be a copolymer with other structural units, or may include a precursor of the structural unit represented by general formula (1) (polyamic acid structure).
  • the structural unit represented by general formula (1) is preferably contained in an amount of no less than 50 mol% of the total amount of the polyimide.
  • the type and the amount of a structural unit used for copolymerization or mixing are preferably selected within the bounds of not deteriorating the heat resistance of a polyimide obtained by a final heating treatment.
  • the imidization ratio of the polyimide (a) can be easily determined by the following method.
  • the imidization ratio means a mole percentage of a polyimide precursor converted into a polyimide in synthesis of a polyimide through a polyimide precursor as described above.
  • the infrared spectrum of a polyimide precursor is measured, and the presence of absorption peaks (around 1780 cm -1 and around 1377 cm -1 ) originating from a polyimide is confirmed.
  • the polyimide precursor is subjected to a heat treatment at 350°C for an hour, the infrared spectrum is then measured again, and peak intensities around 1377 cm -1 before and after the heat treatment are compared.
  • the imidization ratio of the polymer before the heat treatment is determined with the imidization ratio of the polymer after the heat treatment set to 100%.
  • the imidization ratio of the polyimide (a) is preferably not less than 90%.
  • the end capping agent introduced into the polyimide (a) can be detected by the following method.
  • a polyimide, into which an end capping agent is introduced is dissolved in an acidic solution to be decomposed into an amine component and a carboxylic anhydride component that are constituent units of the polyimide, and these components are analyzed by gas chromatography (GC) or NMR.
  • GC gas chromatography
  • NMR nuclear magnetic resonance
  • a polyimide, into which an end capping agent is introduced is directly analyzed using a pyrolysis gas chromatograph (PGC) or an infrared spectrum and a 13 CNMR spectrum.
  • PPC pyrolysis gas chromatograph
  • the weight average molecular weight of the polyimide (a) should be 10000 to 100000 inclusive.
  • the weight average molecular weight of at least one thereof is preferably in the range described above. If the weight average molecular weight is less than 10000, the mechanical strength may significantly decrease, leading to a reduction in adhesion strength.
  • the weight average molecular weight is preferably not less than 12000.
  • the weight average molecular weight is more than 100000, the solubility in an alkali development liquid may decrease, leading to occurrence of development residues.
  • the weight average molecular weight is preferably not more than 50000.
  • the weight average molecular weight in the present invention is measured by gel permeation chromatography (GPC), and calculated in terms of polystyrene.
  • the photosensitive resin composition of the present invention preferably contains (b) a compound having two or more epoxy groups and/or oxetanyl groups in each molecule, wherein the compound (b) is a compound having two or more epoxy groups.
  • the compound having two or more epoxy groups in each molecule include a bisphenol A-type epoxy compound, a bisphenol F-type epoxy compound, a novolac-type epoxy compound, a biphenol-type epoxy compound, a biphenyl-type epoxy compound, a glycidyl amine-type epoxy compound and a cyclic aliphatic epoxy compound.
  • the compound having two or more oxetanyl groups in each molecule include OXT-121, OXT-221, OX-SQ-H, OXT-191, PNOX-1009 and RSOX (manufactured by Toagosei Co., Ltd.), and "ETERNACOLL” OXBP and OXTP (manufactured by UBE INDUSTRIES, LTD.).
  • the content of the compound (b) should be not less than 20 parts by weight, more preferably not less than 40 parts by weight, per 100 parts by weight of the polyimide (a).
  • the content of the compound (b) is preferably not more than 100 parts by weight per 100 parts by weight of the polyimide (a) from the viewpoint of the heat resistance and development characteristic.
  • the photosensitive resin composition of the present invention contains a naphthoquinonediazide compound (c).
  • the naphthoquinonediazide compound used is not particularly limited, but one example is a compound with a naphthoquinonediazidesulfonic acid ester-bonded to a compound having a phenolic hydroxyl group.
  • a compound having two or more phenol cores in each molecule is preferably used.
  • the naphthoquinonediazide compound can be synthesized by a publicly known esterification reaction of a compound having a phenolic hydroxyl group and a naphthoquinonediazidesulfonic acid chloride.
  • Specific examples of the compound having a phenolic hydroxyl group include the following compounds (all manufactured by Honshu Chemical Industry Co., Ltd.).
  • TekP-4HBPA TrisP-HAP
  • TrisP-PA TrisP-PA
  • Phcc-AP are preferably used from the viewpoint of the sensitivity and resolution.
  • the naphthoquinonediazidesulfonic acid chloride as a raw material, 4-naphthoquinonediazidesulfonic acid chloride or 5-naphthoquinonediazidesulfonic acid chloride can be used.
  • the 4-naphthoquinonediazidesulfonate compound has an absorption in an i-line (wavelength: 365 nm) range, and is therefore suitable for i-line exposure.
  • the 5-naphthoquinonediazidesulfonate compound has an absorption in a wide wavelength range, and is therefore suitable for exposure in a wide wavelength range.
  • the 4-naphthoquinonediazidesulfonate compound or the 5-naphthoquinonediazidesulfonate compound can also be mixed and used. There are preferably two or more naphthoquinonediazidesulfonate structures from the viewpoint of the resolution.
  • the added amount of the naphthoquinonediazide compound is not particularly limited, but is preferably 5 to 40 parts by weight, further preferably 10 to 30 parts by weight, per 100 parts by weight of the polyimide (a).
  • the added amount of the naphthoquinonediazide compound is preferably not less than 5 parts by weight for obtaining a still better dissolution contrast.
  • the added amount of the naphthoquinonediazide compound is more than 40 parts by weight, a film or a cured film formed using a photosensitive resin composition may become fragile.
  • the photosensitive resin composition of the present invention may contain an acrylic resin.
  • the acrylic resin used herein is a polymer of an unsaturated carboxylic acid, an unsaturated carboxylate or the like, which is the acrylic resin described in Japanese Patent Laid-open Publication No. 2009-20246 , and so on.
  • the acrylic resin is contained in a large amount, the heat stability is degraded at 250°C or higher, so that the reliability is impaired.
  • the film after drying off a solvent becomes fragile, so that it is very difficult to form the composition into a B stage film.
  • the content of the acrylic resin is preferably less than 10 parts by weight per 100 parts by weight of the polyimide (a), and preferably substantially no acrylic resin is contained particularly when the photosensitive resin composition of the present invention is used as a film.
  • the photosensitive resin composition of the present invention may contain a surfactant, inorganic particles such as silicon dioxide and titanium dioxide, additives such as a crosslinker, a crosslinking accelerator, a sensitizer, a dissolution adjustor, a stabilizer and an anti-foaming agent, a silane coupling agent, a titanium chelating agent, a zirconia chelating agent and so on.
  • a surfactant such as silicon dioxide and titanium dioxide
  • additives such as a crosslinker, a crosslinking accelerator, a sensitizer, a dissolution adjustor, a stabilizer and an anti-foaming agent, a silane coupling agent, a titanium chelating agent, a zirconia chelating agent and so on.
  • organic solvent it is preferable to add an organic solvent to the photosensitive resin composition of the present invention.
  • the organic solvent used should be one that is capable of dissolving or dispersing the components.
  • organic solvent examples include ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether and ethylene glycol dibutyl ether; acetates such as ethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate, propyl acetate, butyl acetate, isobutyl acetate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, methyl lactate, ethyl lactate and butyl lactate; ketones such as acetone, methyl ethyl ketone, acetylacetone, methyl propyl ketone, methyl butyl ketone, methyl isobutyl ketone, cyclopentanone and 2-heptanone and 2-
  • the photosensitive resin composition may be filtered using a filter paper or a filter.
  • the method for filtration is not limited, but mention is made of a method of filtering the composition by filtration under pressure using a membrane filter with a retention particle diameter of 0.2 ⁇ m to 10 ⁇ m.
  • the shape before curing is not limited, and mention is made of, for example, a varnish shape and a film shape.
  • the film shape may be a shape of a sheet formed on a support.
  • a solution obtained by dissolving in an organic solvent the components (a) to (c) and components added as necessary can be used.
  • a photosensitive resin composition film is obtained by applying the photosensitive resin composition of the present invention onto a support, and then drying the applied composition as necessary.
  • a laminate of the present invention has a support, the photosensitive resin composition film of the present invention and a cover film in this order.
  • the photosensitive resin composition film of the present invention is preferably formed on a support.
  • the support used in the laminate of the present invention is not particularly limited, but various kinds of films that are usually commercially available, such as a polyethylene terephthalate (PET) film, a polyethylene film, a polypropylene (PP) film, a polyphenylene sulfide film and a polyimide film, can be used.
  • PET polyethylene terephthalate
  • PP polypropylene
  • the surface of the support may be treated with silicone, a silane coupling agent, an aluminum chelating agent, polyurea and so on for adjusting a wetting property, an adhesion property and a release property with the photosensitive resin composition.
  • the thickness of the support is not particularly limited, but is preferably in a range of 10 to 100 ⁇ m from the viewpoint of a working property.
  • the photosensitive resin composition film of the present invention may have a cover film on the photosensitive resin composition film for protecting the surface.
  • the cover film include a polyethylene film, a polypropylene (PP) film and a polyester film.
  • the cover film has preferably a low adhesion force with a photosensitive adhesive film.
  • the method for forming the laminate of the present invention include a method in which the photosensitive resin composition of the present invention is applied onto a film of a support, and dried, and a cover film is laminated to the surface of the photosensitive resin composition film.
  • Examples of the method for applying the photosensitive resin composition to the support include spin coating using a spinner, spray coating, roll coating, screen printing, blade coating, die coating, calender coating, meniscus coating, bar coating, roll coating, comma roll coating, gravure coating, screen coating and slit die coating.
  • the coating film thickness varies depending on the coating method, the solid concentration of the composition, the viscosity and so on, but normally the film thickness after drying is preferably 0.5 ⁇ m to 80 ⁇ m inclusive.
  • drying an oven, a hot plate, an infrared oven or the like can be used.
  • the drying temperature and the drying time should be in a range which allows an organic solvent to be volatilized, and it is preferable to appropriately conditions which ensure that the photosensitive resin composition film is in an uncured or semi-cured state.
  • drying is preferably carried out at a temperature in a range of 40°C to 120°C for one minute to several tens of minutes. These temperatures may be combined to elevate the temperature, and for example, a heat treatment may be carried out at 70°C, 80°C and 90°C for one minute for each temperature.
  • a photosensitive resin composition coating is formed on a substrate using the photosensitive resin composition of the present invention and the photosensitive resin composition film using the same.
  • the photosensitive resin composition is applied onto a substrate, and dried as necessary, whereby a coating can be formed.
  • the coating method include spin coating using a spinner, spray coating, roll coating and screen printing.
  • the coating film thickness varies depending on the coating method, the solid concentration of the resin composition, the viscosity and so on, but normally it is preferable to apply the composition so that the film thickness after drying is 0.5 ⁇ m to 80 ⁇ m inclusive.
  • an oven, a hot plate, an infrared oven or the like can be used.
  • the drying temperature and the drying time should be in a range which allows an organic solvent to be volatilized, and it is preferable to appropriately set a range which ensures that the photosensitive resin composition coating is in an uncured or semi-cured state. Specifically, drying is preferably carried out at a temperature in a range of 50°C to 150°C for one minute to several hours.
  • the cover film is peeled off, and the photosensitive resin composition film and the substrate are laminated together by thermocompression such that the former and the latter are opposite to each other.
  • Thermocompression can be performed by a heat press process, a heat lamination process, a heat vacuum lamination process or the like.
  • the laminating temperature is preferably not lower than 40°C from the viewpoint of conformability to raised and recessed portions of the substrate.
  • the laminating temperature is preferably not higher than 150°C for preventing deterioration of the pattern resolution due to curing of the photosensitive resin composition film at the time of laminating.
  • the substrate examples include, but are not limited to, a silicon wafer, a ceramic, gallium arsenide, an organic circuit substrate, an inorganic circuit substrate, and these substrates on which circuit constituent materials are placed.
  • the organic circuit substrate include glass base copper-clad laminates such as a glass fabric/epoxy copper-clad laminate, composite copper-clad laminates such as a glass nonwoven fabric/epoxy copper-clad laminate, heat-resistant/thermoplastic substrates such as a polyether imide resin substrate, a polyether ketone resin substrate and a polysulfone-based resin substrate, and flexible substrates such as a polyester copper-clad film substrate and a polyimide copper-clad film substrate.
  • the inorganic circuit substrate examples include ceramic substrates such as an aluminum substrate, an aluminum nitride substrate and a silicon carbide substrate, and metal-based substrates such as an aluminum base substrate and an iron base substrate.
  • the circuit constituent material include conductors containing metals such as silver, gold, copper and aluminum, resistors containing an inorganic oxide and so on, low dielectric materials containing a glass-based material and/or a resin and so on, high dielectric materials containing a resin, inorganic particles having a high dielectric constant, and so on, and insulators containing a glass-based material and so on.
  • the photosensitive resin composition coating formed by the above-mentioned method is irradiated with exposure light through a mask having a predetermined pattern to perform exposure.
  • an exposure light source an i-line (365 nm), an h-line (405 nm) and a g-line (436 nm) of a mercury lamp are preferably used.
  • the photosensitive resin composition film may be exposed without peeling off the support from the photosensitive resin composition film if the support is a material that is transparent to these rays.
  • a stepper type exposure system or a mask aligner, a mirror projection type exposure system or the like can be used.
  • the developer is preferably an aqueous solution of tetramethyl ammonium, or an aqueous solution of an alkaline compound such as diethanolamine, diethylaminoethanol, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, triethylamine, diethylamine, methylamine, dimethylamine, dimethylaminoethyl acetate, dimethylaminoethanol, dimethylaminoethyl methacrylate, cyclohexylamine, ethylenediamine or hexamethylenediamine.
  • an alkaline compound such as diethanolamine, diethylaminoethanol, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, triethylamine, diethylamine, methylamine, dimethylamine, dimethylaminoethyl acetate, dimethylaminoethanol, dimethylaminoethyl methacrylate, cyclohexylamine, ethylenediamine or
  • one of polar solvents such as N-methyl-2-pyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, ⁇ -butyrolactone and dimethylacrylamide, alcohols such as methanol, ethanol and isopropanol, esters such as ethyl lactate and propylene glycol monomethyl ether acetate, and ketones such as cyclopentanone, cyclohexanone, isobutyl ketone and methyl isobutyl ketone, or a combination of several kinds thereof may be included in the aforementioned aqueous alkali solution.
  • polar solvents such as N-methyl-2-pyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, ⁇ -butyrolactone and dimethylacrylamide
  • alcohols such as methanol, ethanol and isopropanol
  • esters such as
  • Development can be performed by a method in which the developer is sprayed to the surface of the coating, a method in which the developer is deposited on the surface of the coating, a method in which the film is immersed in the developer, a method in which the film is immersed and subjected to ultrasonication, or the like.
  • Development conditions such as the development time, the development step and the temperature of the developer should be conditions which ensure that exposed areas can be removed to form a pattern.
  • the developer is preferably rinsed with water after development.
  • the developer may be rinsed with water plus an alcohol such as ethanol or isopropyl alcohol, an ester such as ethyl lactate or propylene glycol monomethyl ether acetate, or the like.
  • a baking treatment may be carried out as necessary before development. Consequently, the resolution of the pattern after development is improved, or the allowable range of development conditions is increased in some cases.
  • the temperature of the baking treatment is preferably in a range of 50 to 180°C, more preferably in a range of 60 to 120°C in particular.
  • the time is preferably 5 seconds to several hours.
  • a quinonediazide compound After formation of a pattern, a quinonediazide compound remains in the photosensitive resin composition coating. Therefore, the compound may be thermally decomposed to produce nitrogen at the time of thermodecompression or curing.
  • the entire surface of the photosensitive resin composition coating after formation of a pattern is preferably irradiated with the above-mentioned exposure light to decompose the quinonediazide compound beforehand. This process is referred to as bleaching exposure.
  • the photosensitive resin composition coating is dried by heating at a temperature in a range of 60 to 200°C for reducing a solvent, a volatile component, water, nitrogen and so on that remain in the photosensitive resin composition coating.
  • the time is preferably one minute to several hours.
  • the substrate provided with the photosensitive resin composition coating, on which a pattern is formed, is thermally compressed on a substrate or any other member to be temporarily fixed.
  • the thermocompression temperature is preferably in a temperature range of 100 to 150°C.
  • the pressure during thermocompression is preferably in a range of 0.01 to 10 MPa.
  • the time is preferably one second to several minutes. Thermocompression may be performed under normal pressure, or may be performed in vacuum for prevention of trapping of air bubbles and so on.
  • the photosensitive resin composition coating is formed into a cured film by heating at a temperature of 120°C to 400°C.
  • a temperature is selected and elevated stepwise, or a certain temperature range is selected, and the temperature is continuously elevated for 5 minutes to 5 hours.
  • the heat treatment is carried out at 130°C and 200°C for 30 minutes for each temperature.
  • the heating temperature is preferably 150°C to 300°C inclusive, and further preferably 180°C to 250°C inclusive.
  • the heating treatment may be performed under normal pressure, or may be performed in vacuum.
  • the adhesion strength of the bonded object after curing is preferably not less than 30 MPa from the viewpoint of adhesion reliability. More preferable is no less than 45 MPa.
  • the film thickness of the cured film can be arbitrarily set, but is preferably 0.5 ⁇ m to 80 ⁇ m inclusive.
  • a semiconductor device having a photosensitive resin composition cured film will now be described as an application of the photosensitive resin composition and the photosensitive resin composition film of the present invention.
  • semiconductor devices of various structures have been proposed, and the application of the photosensitive resin composition of the present invention is not limited to those described below.
  • the photosensitive resin composition and the photosensitive resin composition film of the present invention can be suitably used as an adhesive for a semiconductor for bonding, fixing and sealing a semiconductor element, a semiconductor device, a circuit substrate and a metal wiring material.
  • the photosensitive resin composition and the photosensitive resin composition film of the present invention can also be used as an insulating film for a semiconductor element, a semiconductor device, a circuit substrate and so on.
  • the semiconductor device in the present invention refers to not just a product prepared by bonding a semiconductor element to a substrate, and a product prepared by bonding semiconductor elements or bonding substrates, but refers to all devices that can function by utilizing the properties of semiconductor elements, and electro-optic devices, semiconductor circuit substrates and electronic components including them are all encompassed in the semiconductor device.
  • One example of the method for producing a semiconductor device using the photosensitive resin composition and the photosensitive resin composition film of the present invention is as follows.
  • a first circuit member having a first jointing terminal and a second circuit member having a second jointing terminal are placed such that the first jointing terminal and the second jointing terminal are opposite to each other.
  • the photosensitive resin composition film of the present invention is interposed between the first jointing terminal and the second jointing terminal placed opposite to each other to form a photosensitive resin composition coating.
  • a varnish of the photosensitive resin composition is applied to any one or both of the surface of the first jointing terminal and the second jointing terminal, and dried to thereby form a photosensitive resin composition coating.
  • the photosensitive resin composition coating is patterned to open an area where conduction should be provided between the first jointing terminal and the second jointing terminal. Thereafter, the first circuit member and the second circuit member are heated and compressed to electrically connect these circuit members.
  • Electrical connection may be performed after first forming the photosensitive resin composition coating on the surface of only any one of the circuit members at the jointing terminal side, or may be performed after forming the photosensitive resin composition coating on the surfaces of both the first and second circuit members at the jointing terminal side.
  • a through electrode may be formed on the first circuit member and/or the second circuit member, and the jointing terminal may be formed on one surface and/or both the surfaces of the member.
  • a chip component such as a semiconductor chip provided with bumps such as a plated bump and a stud bump, a chip Resistor or a chip condenser, a semiconductor chip having a TSV (through silicon via) electrode, or a silicon interposer, a substrate such as a glass epoxy circuit substrate or a film circuit substrate, or the like is used.
  • a semiconductor device with circuit members laminated three-dimensionally is obtained by repeatedly performing such connection as described above using circuit members having jointing terminals on both the surfaces.
  • a semiconductor device in which the edge of an adhesive after curing is located at the inner side as compared to the edge of a circuit member, i.e. a semiconductor device in which occurrence of protrusion of an adhesive (fillet) to the outer periphery of circuit members is suppressed after a first circuit member and a second circuit member are heated and compressed.
  • a semiconductor device in which occurrence of protrusion of an adhesive (fillet) to the outer periphery of circuit members is suppressed after a first circuit member and a second circuit member are heated and compressed.
  • One example of the method for producing a semiconductor device in which occurrence of the fillet is suppressed is as follows.
  • a photosensitive resin composition coating is formed between a first circuit member and a second circuit member in the same manner as in the above-mentioned method for producing a semiconductor device.
  • the photosensitive resin composition coating at the peripheral part of the first circuit member and/or the second circuit member is removed by patterning the photosensitive resin composition coating.
  • the first circuit member and the second circuit member are heated and compressed to bond these circuit members.
  • a semiconductor device in which a cured product of the photosensitive resin composition coating does not protrude from the first circuit member and the second circuit member.
  • a photosensitive resin composition film is attached, or a varnish of a photosensitive resin composition is applied and dried to thereby form a photosensitive resin composition coating.
  • the photosensitive resin composition coating is patterned, and then a glass substrate is laminated on a left pattern as a support substrate, and thermally compressed. The laminate is heated to cure the photosensitive resin composition coating.
  • an image sensor having a hollow structure, wherein a semiconductor element and a glass substrate are bonded with a cured product of the patterned photosensitive resin composition coating as a barrier wall.
  • a method for preparing a photosensitive resin composition of the present invention and a method for producing a photosensitive resin composition sheet, and a method for evaluating the properties thereof and the results will be described more specifically below, but the present invention is not limited thereto.
  • a polyimide was dissolved in NMP to prepare a solution having a solid concentration of 0.1% by weight, and a weight average molecular weight was calculated in terms of polystyrene by a GPC apparatus Waters 2690 (manufactured by Waters Co., Ltd.) having a configuration shown below.
  • the mobile layer was NMP with LiCl and phosphoric acid each dissolved therein at a concentration of 0.05 mol/L, and the development rate was 0.4 ml/minute.
  • the column was warmed to 40°C using a column oven.
  • Detector Waters 996 System controller: Waters 2690 Column: TOSOH TSK-GEL ⁇ -4000 Column: TOSOH TSK-GEL ⁇ -2500
  • the infrared spectrum of a polyimide was measured, and the presence of absorption peaks (around 1780 cm -1 and around 1377 cm -1 ) originating from an imide structure in the polyimide was confirmed.
  • the polyimide was subjected to a heat treatment at 350°C for an hour, the infrared spectrum is then measured again, and peak intensities around 1377 cm -1 before and after the heat treatment were compared.
  • the imidization ratio of the polyimide before the heat treatment was determined with the imidization ratio of the polyimide after the heat treatment set to 100%.
  • a photosensitive resin composition prepared in each of Examples and Comparative Examples was applied by spin coating onto a silicon wafer using a spin coater.
  • the rotation time was 10 seconds, and the number of rotations was adjusted to about 500 to 700 rpm so that the film thickness after drying was about 25 ⁇ m.
  • the photosensitive resin composition was dried for 3 minutes on a hot plate at 100°C after being applied.
  • a cover film of a photosensitive resin composition film prepared in each of Examples and Comparative Examples was peeled off, the peeled surface was laminated onto a silicon wafer under conditions of stage temperature: 80°C; roll temperature: 80°C; degree of vacuum: 150 Pa; attaching rate: 5 mm/second; and attaching pressure: 0.2 Mpa using a lamination apparatus (VTM-200M manufactured by Takatori Corporation), and a support film was peeled off.
  • the exposure gap between the mask and the photosensitive resin composition film was 100 ⁇ m, and L39 filter transmitted light from an ultra-high pressure mercury lamp was applied in an amount of 400 mJ/cm 2 (photometric value in an h-line).
  • exposed areas were removed using a 2.38% aqueous solution of tetramethylammonium hydroxide in dip development, and rinsing was carried out with water.
  • the development time was 1.5 times as long as the time taken for exposed areas to be fully dissolved.
  • the obtained pattern was observed with an optical microscope, and a minimum size with defects such as clogging being absent in lines of the pattern was evaluated as a resolution.
  • a silicon wafer laminated or applied by spin coating onto a silicon wafer was exposed in an exposure amount of 1000 mJ/cm 2 (photometric value in an i-line) using an ultra-high pressure mercury lamp in the manner described above, and then heat-treated under an atmosphere of N 2 at 200°C for 60 minutes in an inert oven (INL-60 manufactured by Koyo Thermo Systems Co., Ltd.) to obtain a cured film.
  • the obtained cured film on the silicon wafer was immersed in 47% hydrofluoric acid at room temperature for 7 minutes, and then washed with tap water, and the cured film was peeled off from the silicon wafer.
  • a thermal weight loss was measured under a condition of temperature elevation rate: 10°C under a nitrogen atmosphere using an apparatus for thermogravimetry (TG/DTA 6200 manufactured by SII NanoTechnology Inc.), and a temperature at which the weight loss was 1% with respect to a weight at the start of measurement was designated as an indicator of the heat resistance.
  • a silicon wafer laminated or applied by spin coating onto a silicon wafer was exposed in an exposure amount of 400 mJ/cm 2 (photometric value in an h-line) in the manner as described above.
  • the silicon wafer after exposure was cut into 50 x 50 mm, placed on a hot plate at 150°C with the photosensitive resin composition film at the upper side, and preliminarily heated for one minute, and a silicon chip (2 ⁇ 2 mm, thickness: 525 ⁇ m) was then thermally compressed at a pressure of 0.2 MPa for 30 seconds to be temporarily fixed.
  • a warp of a 6-inch silicon wafer was measured by a stress measurement apparatus and to this wafer, the photosensitive resin composition film was laminated or the photosensitive resin composition was applied by spin coating.
  • This silicon wafer was exposed in an exposure amount of 1000 mJ/cm 2 (photometric value in an i-line) using an ultra-high pressure mercury lamp, and then heat-treated under an atmosphere of N 2 at 200°C for 60 minutes in an inert oven (INL-60 manufactured by Koyo Thermo Systems Co., Ltd.) to obtain a cured film.
  • a warp of the substrate after curing was measured by the stress measurement apparatus again, and a stress at room temperature was calculated from warps of the wafer before and after formation of the cured film.
  • a polyimide and a quinolinediazide compound used in each of Examples and Comparative Examples were synthesized by the following method.
  • NMP N-methyl-2-pyrrolidone
  • 4,4'-DAE 4,4'-diaminodiphenyl ether
  • SiDA 1,3-bis (3-aminopropyl) tetramethyldisiloxane
  • MAP 3-aminophenol
  • the resin solution was poured in 3 L of water to collect white precipitates.
  • the precipitates were collected by filtration, washed with water three times, and then dried in a vacuum dryer at 80°C for 5 hours to obtain polyimide B.
  • the imidization ratio of the obtained resin powder was 94%.
  • NMP N-methyl-2-pyrrolidone
  • 4,4'-DAE 4,4'-diaminodiphenyl ether
  • SiDA 1,3-bis (3-aminopropyl) tetramethyldisiloxane
  • MAP 3-aminophenol
  • a triethylamine salt was filtered, and the filtrate was poured in water. Thereafter, deposited precipitates were collected by filtration, and further washed with 1 L of 1% aqueous hydrochloric acid. Thereafter, the precipitates were further washed with 2 L of water twice. The precipitates were dried in a vacuum dryer to obtain quinonediazide compound A represented by the following formula.
  • a triethylamine salt was filtered, and the filtrate was poured in water. Thereafter, deposited precipitates were collected by filtration, and further washed with 1 L of 1% aqueous hydrochloric acid. Thereafter, the precipitates were further washed with 2 L of water twice. The precipitates were dried in a vacuum dryer to obtain quinonediazide compound B represented by the following formula.
  • the obtained photosensitive adhesive was applied onto a PET film having a thickness of 38 ⁇ m using a comma roll coater, and dried at 75°C for 6 minutes, and a PP film having a thickness of 10 ⁇ m was then laminated as a cover film to obtain a photosensitive resin composition film. Coating was performed so that the film thickness of the photosensitive resin composition film was about 25 ⁇ m.
  • the obtained photosensitive adhesive film was used to evaluate the resolution, the heat resistance, the adhesion strength and the stress in the manner described previously.
  • a photosensitive resin composition film was prepared in the mixing ratio shown in Table 1 in the same manner as in Example 1, and the resolution, the heat resistance, the adhesion strength and the stress were evaluated in the manner described previously.
  • the photosensitive resin composition of Example 1 was applied by spin coating to a silicon wafer by the method described above to form a coated film.
  • the obtained product was used to evaluate the resolution, the heat resistance, the adhesion strength and the stress.
  • the photosensitive resin composition of Example 3 was applied by spin coating to a silicon wafer by the method described above to form a coated film.
  • the obtained product was used to evaluate the resolution, the heat resistance, the adhesion strength and the stress.
  • a photosensitive resin composition film was prepared in the mixing ratio shown in Table 2 in the same manner as in Example 1, and the resolution, the heat resistance, the adhesion strength and the stress were evaluated in the manner described previously.
  • a photosensitive resin composition was prepared in accordance with the composition described in Table 2, and an attempt was made to form a photosensitive resin composition film in the same manner as in Example 1, but cracks occurred in a film state because the film was fragile, so that the resolution, the adhesion strength and the stress could not be evaluated. For the film after curing, only the heat resistance was evaluated.
  • the photosensitive resin composition of Reference Example 1 was applied by spin coating to a silicon wafer by the method described above to form a coated film.
  • the obtained product was used to evaluate the resolution, the heat resistance, the adhesion strength and the stress.
  • the resistance value was kept at 10 10 ⁇ up to 1000 hours, and therefore the sample was considered acceptable for the insulation reliability.
  • the copper comb Electrode such an electrode was used that on a silicon wafer on which a thermal oxide film having a thickness of 0.4 ⁇ m was formed and a silicon nitride film having a thickness of 0.8 ⁇ m was formed thereon, a chromium ground electrode having a thickness of 0.08 ⁇ m was pattern-formed and a copper electrode having a thickness of 10 ⁇ m was pattern-formed thereon.
  • a Ni layer (10 nm) as an adhesive layer 101 was formed on a silicon wafer 100 and an electroless copper plated layer (10 ⁇ m) as a conductor layer 102 was formed thereon by sputtering.
  • the photosensitive adhesive varnish obtained in Example 2 was applied by spin coating onto the substrate using a spin coater, and dried to form a photosensitive resin composition coating. Thereafter, a via hole was formed in the photosensitive resin composition coating by exposure and development, and the photosensitive resin composition coating was cured by carrying out a heating treatment in an inert oven to obtain a substrate having a via hole layer 102 ( Fig. 1 (a) ).
  • the photosensitive resin composition varnish obtained in Example 2 was applied by spin coating to the substrate using a spin coater, a pattern (space area) forming a wiring hole layer was formed by drying, exposure and development, and the wiring hole layer 103 was cured by carrying out a heating treatment in an inert oven to obtain a substrate having a via hole/wiring hole ( Fig. 1 (b) ).
  • a Ni layer (thickness: 10 nm) as an adhesive layer was formed on the substrate by sputtering, and electrolytic copper plating was performed to fill the via hole and the wiring hole with copper plating. Thereafter, copper plating of unwanted areas were removed and the surface of an insulating film was flattened by chemical mechanical polishing (CMP) to obtain a substrate having a via layer/wiring layer 104 ( Fig. 1 (c) ).
  • CMP chemical mechanical polishing
  • EP4003S Propylene oxide-modified BisA type epoxy resin (manufactured by ADEKA Corporation) jER152: Phenol novolac epoxy resin (manufactured by Mitsubishi Chemical Corporation) jER630: Glycidylamine type epoxy resin (manufactured by Mitsubishi Chemical Corporation) NC3000: Biphenyl type epoxy resin (manufactured by Nippon Kayaku Co., Ltd.) "EPICLON (registered trademark)" 850S: BisA type epoxy resin (manufactured by DIC Corporation)
  • a photosensitive resin composition and a photosensitive resin composition film each of which is capable of forming a positive tone pattern by photolithography, has small stress after curing, and exhibits a high strength of adhesion with a semiconductor element and a support member.

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EP11800602.2A 2010-07-02 2011-06-10 Composition de résine photosensible, pellicule de composition de résine photosensible, et dispositif semi-conducteur utilisant la composition de résine photosensible ou la pellicule de composition de résine photosensible Not-in-force EP2590025B1 (fr)

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Cited By (4)

* Cited by examiner, † Cited by third party
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EP2857470A4 (fr) * 2012-05-30 2016-02-17 Toray Industries Feuille adhésive pour la fabrication d'un dispositif semi-conducteur ayant des électrodes à bosse et procédé de fabrication du dispositif semi-conducteur
EP2902846A4 (fr) * 2012-09-24 2016-06-01 Toray Industries Composition de résine photosensible positive
KR20160079356A (ko) 2014-12-26 2016-07-06 도레이케미칼 주식회사 포지티브형 감광성 폴리아미드 수지, 이의 조성물 및 이를 제조하는 방법
US10639876B2 (en) 2014-07-18 2020-05-05 Eternal Materials Co., Ltd. Solvent-containing dry film and method for applying the same on a substrate

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101998449B1 (ko) * 2012-03-26 2019-07-09 도레이 카부시키가이샤 감광성 흑색 수지 조성물 및 수지 블랙 매트릭스 기판
TW201413387A (zh) * 2012-09-26 2014-04-01 Toray Industries 正型感光性樹脂組成物
WO2015008330A1 (fr) * 2013-07-16 2015-01-22 日立化成株式会社 Composition de résine photosensible, adhésif en film, feuille adhésive, motif d'adhésif, tranche semi-conductrice avec couche adhésive, et dispositif à semi-conducteurs
KR102399270B1 (ko) * 2014-11-27 2022-05-19 도레이 카부시키가이샤 수지 및 감광성 수지 조성물
KR102456965B1 (ko) * 2015-03-04 2022-10-21 도레이 카부시키가이샤 감광성 수지 조성물, 수지 경화막의 제조 방법 및 반도체 장치
JPWO2017043375A1 (ja) * 2015-09-08 2018-06-21 東レ株式会社 感光性樹脂組成物、感光性シート、半導体装置および半導体装置の製造方法
JP7112827B2 (ja) * 2015-12-25 2022-08-04 旭化成株式会社 感光性樹脂組成物、感光性樹脂積層体、樹脂パターン製造方法、硬化膜パターン製造方法及び表示装置
TWI583266B (zh) * 2016-06-30 2017-05-11 欣興電子股份有限公司 線路板及其製作方法
KR101865873B1 (ko) * 2016-11-09 2018-06-11 해성디에스 주식회사 반도체 패키지 기판의 제조 방법
KR20180081273A (ko) * 2017-01-06 2018-07-16 쌍신전자통신주식회사 플렉시블 습도 센서 및 그 제조방법
JP6526146B2 (ja) * 2017-10-23 2019-06-05 藤森工業株式会社 接着性樹脂組成物、接着性樹脂成形体、及び接着性樹脂積層体
US10535617B2 (en) * 2018-05-10 2020-01-14 International Business Machines Corporation Implementing transient electronic circuits for security applications
TWI810437B (zh) 2019-03-05 2023-08-01 日商住友電木股份有限公司 含有反應性端基之聚醯亞胺、聚醯胺酸及其感光性組成物
WO2020181022A1 (fr) 2019-03-05 2020-09-10 Promerus, Llc Acides polyamiques et polyimides coiffés par anhydride cyclique insaturé terminal et compositions photosensibles associées
WO2020181021A1 (fr) 2019-03-05 2020-09-10 Promerus, Llc Compositions de polyimide photosensibles
JP7565088B2 (ja) * 2019-06-06 2024-10-10 株式会社ピーアイ技術研究所 感光性ポリイミド樹脂組成物
TWI782241B (zh) * 2019-11-12 2022-11-01 臺灣永光化學工業股份有限公司 聚醯亞胺正型光阻組成物
WO2023085325A1 (fr) * 2021-11-10 2023-05-19 株式会社カネカ Composition de résine, corps moulé et film
CN114196015A (zh) * 2021-12-13 2022-03-18 吉林奥来德光电材料股份有限公司 一种光敏聚酰亚胺树脂前体及制备方法、光敏聚酰亚胺树脂前体组合物、光敏聚酰亚胺膜
TW202428827A (zh) * 2022-09-21 2024-07-16 日商積水化學工業股份有限公司 樹脂組成物、暫時固定材、及電子零件之製造方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090075198A1 (en) * 2007-02-09 2009-03-19 Sony Chemical & Information Device Corporation Photosensitive Polyimide Resin Composition
US20100035182A1 (en) * 2007-04-10 2010-02-11 Nippon Kayaku Kabushiki Kaisha Photosensitive resin composition

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH04337380A (ja) 1991-05-15 1992-11-25 Sumitomo Bakelite Co Ltd 耐熱感光性ポリイミド接着剤
JPH06308730A (ja) * 1993-04-26 1994-11-04 Chisso Corp 感光性ポリイミド前駆体組成物
US20040235992A1 (en) * 2001-05-30 2004-11-25 Koji Okada Photosensitive resin composition and photosensitive dry film resist and photosensitive coverlay film produced therefrom
KR101150593B1 (ko) 2004-03-12 2012-06-01 도레이 카부시키가이샤 포지티브형 감광성 수지 조성물, 이를 이용한 릴리프 패턴, 및 고체 촬상 소자
JP4918968B2 (ja) 2005-05-09 2012-04-18 日立化成デュポンマイクロシステムズ株式会社 ポジ型感光性樹脂組成物、パターンの製造方法及び電子部品
EP1909142B1 (fr) 2005-06-30 2015-06-24 Toray Industries, Inc. Composition de résine photosensible et amplificateur d adhésion
CN102393607B (zh) * 2005-11-30 2013-11-13 住友电木株式会社 正型感光性树脂组合物及使用该组合物的半导体器件和显示器
JP4765951B2 (ja) * 2007-02-08 2011-09-07 Ｊｓｒ株式会社 絶縁膜を有する大型シリコンウエハおよびその製造方法
TW200907578A (en) * 2007-04-10 2009-02-16 Nippon Kayaku Kk Photosensitive resin composition
JP2008281597A (ja) 2007-05-08 2008-11-20 Toray Ind Inc 感光性樹脂組成物シート
JP5040432B2 (ja) 2007-05-15 2012-10-03 住友ベークライト株式会社 感光性樹脂組成物
JP2009020246A (ja) 2007-07-11 2009-01-29 Toray Ind Inc 感光性樹脂組成物、これを用いた絶縁性樹脂パターンの製造方法および有機電界発光素子
US8445621B2 (en) 2007-08-22 2013-05-21 Sony Chemical & Information Device Corporation Polyimide resin and photosensitive polyimide resin composition
JP5196148B2 (ja) * 2008-06-11 2013-05-15 住友電気工業株式会社 感光性樹脂組成物およびそれを用いたポリイミド樹脂膜、フレキシブルプリント配線板
JP5477527B2 (ja) * 2008-09-30 2014-04-23 日産化学工業株式会社 末端官能基含有ポリイミドを含むポジ型感光性樹脂組成物
CN102186904A (zh) * 2008-10-20 2011-09-14 日本化药株式会社 聚酰亚胺树脂及其组合物

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090075198A1 (en) * 2007-02-09 2009-03-19 Sony Chemical & Information Device Corporation Photosensitive Polyimide Resin Composition
US20100035182A1 (en) * 2007-04-10 2010-02-11 Nippon Kayaku Kabushiki Kaisha Photosensitive resin composition

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of WO2012002134A1 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2857470A4 (fr) * 2012-05-30 2016-02-17 Toray Industries Feuille adhésive pour la fabrication d'un dispositif semi-conducteur ayant des électrodes à bosse et procédé de fabrication du dispositif semi-conducteur
EP2902846A4 (fr) * 2012-09-24 2016-06-01 Toray Industries Composition de résine photosensible positive
US10639876B2 (en) 2014-07-18 2020-05-05 Eternal Materials Co., Ltd. Solvent-containing dry film and method for applying the same on a substrate
KR20160079356A (ko) 2014-12-26 2016-07-06 도레이케미칼 주식회사 포지티브형 감광성 폴리아미드 수지, 이의 조성물 및 이를 제조하는 방법

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WO2012002134A1 (fr) 2012-01-05
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CN102985877A (zh) 2013-03-20
KR101463367B1 (ko) 2014-11-18
EP2590025B1 (fr) 2014-09-17
SG186462A1 (en) 2013-01-30
TW201214048A (en) 2012-04-01
CN102985877B (zh) 2015-06-10
KR20130016375A (ko) 2013-02-14
US8946852B2 (en) 2015-02-03
US20130214379A1 (en) 2013-08-22
KR20130119993A (ko) 2013-11-01
MY162630A (en) 2017-06-30
JP5240363B2 (ja) 2013-07-17
EP2590025A4 (fr) 2013-08-28

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